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Beta-isocupreidine-catalyzed Baylis-Hillman Reaction of Chiral N-boc-alpha-amino Aldehydes

Ayako Nakano, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama

Org Lett. 2006 Nov 9;8(23):5357-60.

PMID: 17078717

Abstract:

[Structure: see text] Beta-isocupreidine (beta-ICD)-catalyzed Baylis-Hillman reaction of chiral N-Boc-alpha-amino aldehydes and 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) takes place without racemization and exhibits the match-mismatch relationship between the substrate and the catalyst. In the case of acyclic amino aldehydes, L-substrates show excellent syn selectivity and high reactivity in contrast to D-substrates. On the other hand, in the case of cyclic amino aldehydes, D-substrates rather than L-substrates show excellent anti selectivity and high reactivity.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP2160896 1,1,1,3,3,3-Hexafluoroisopropyl acrylate 1,1,1,3,3,3-Hexafluoroisopropyl acrylate 2160-89-6 Price
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